A thorough study on the amidation conditions of N-acetyl-l-phenylalanine using TBTU and various bases is reported for the synthesis of 2-(N-acetyl)-l-phenylalanylamido-2-deoxy-d-glucose (NAPA), a promising drug for the treatment of joints diseases. TBTU-mediated diastereoselective amidation reaction with 1,3,4,6-tetra-O-acetyl-β-d-glucosamine always gave racemization of N-acetyl-l-phenylalanine. The stereochemical retention under amidation conditions was studied in detail in the presence of difference bases and via other control experiments, evidencing the possibility to reduce racemization using pyridine as base.

N-Acetyl-l-phenylalanine Racemization during TBTU Amidation: An In-Depth Study for the Synthesis of Anti-Inflammatory 2-(N-Acetyl)-l-phenylalanylamido-2-deoxy-d-glucose (NAPA) / Sturabotti, Elisa; Vetica, Fabrizio; Toscano, Giorgia; Calcaterra, Andrea; Martinelli, Andrea; Migneco, Luisa Maria; Leonelli, Francesca. - In: MOLECULES. - ISSN 1420-3049. - 28:2(2023). [10.3390/molecules28020581]

N-Acetyl-l-phenylalanine Racemization during TBTU Amidation: An In-Depth Study for the Synthesis of Anti-Inflammatory 2-(N-Acetyl)-l-phenylalanylamido-2-deoxy-d-glucose (NAPA)

Sturabotti, Elisa;Vetica, Fabrizio;Toscano, Giorgia;Calcaterra, Andrea
;
Martinelli, Andrea;Migneco, Luisa Maria;Leonelli, Francesca
2023

Abstract

A thorough study on the amidation conditions of N-acetyl-l-phenylalanine using TBTU and various bases is reported for the synthesis of 2-(N-acetyl)-l-phenylalanylamido-2-deoxy-d-glucose (NAPA), a promising drug for the treatment of joints diseases. TBTU-mediated diastereoselective amidation reaction with 1,3,4,6-tetra-O-acetyl-β-d-glucosamine always gave racemization of N-acetyl-l-phenylalanine. The stereochemical retention under amidation conditions was studied in detail in the presence of difference bases and via other control experiments, evidencing the possibility to reduce racemization using pyridine as base.
2023
racemization; N-acetyl amino acids; coupling; TBTU; pyridine
01 Pubblicazione su rivista::01a Articolo in rivista
N-Acetyl-l-phenylalanine Racemization during TBTU Amidation: An In-Depth Study for the Synthesis of Anti-Inflammatory 2-(N-Acetyl)-l-phenylalanylamido-2-deoxy-d-glucose (NAPA) / Sturabotti, Elisa; Vetica, Fabrizio; Toscano, Giorgia; Calcaterra, Andrea; Martinelli, Andrea; Migneco, Luisa Maria; Leonelli, Francesca. - In: MOLECULES. - ISSN 1420-3049. - 28:2(2023). [10.3390/molecules28020581]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/1664403
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